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Issue 1, 2015
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Oxidative activation of dihydropyridine amides to reactive acyl donors

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Abstract

Amides of 1,4-dihydropyridine (DHP) are activated by oxidation for acyl transfer to amines, alcohols and thiols. In the reduced form the DHP amide is stable towards reaction with amines at room temperature. However, upon oxidation with DDQ the acyl donor is activated via a proposed pyridinium intermediate. The activated intermediate reacts with various nucleophiles to give amides, esters, and thio-esters in moderate to high yields.

Graphical abstract: Oxidative activation of dihydropyridine amides to reactive acyl donors

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Publication details

The article was received on 11 Sep 2014, accepted on 09 Oct 2014 and first published on 31 Oct 2014


Article type: Paper
DOI: 10.1039/C4OB01931H
Citation: Org. Biomol. Chem., 2015,13, 185-198
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    Oxidative activation of dihydropyridine amides to reactive acyl donors

    E. D. Funder, J. B. Trads and K. V. Gothelf, Org. Biomol. Chem., 2015, 13, 185
    DOI: 10.1039/C4OB01931H

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